Citation: Chen Li, Ziyuan Zhao, Shouyun Yu. Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides[J]. Chinese Chemical Letters, ;2024, 35(6): 109128. doi: 10.1016/j.cclet.2023.109128 shu

Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides

State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China

yushouyun@nju.edu.cn

Received Date: 18 July 2023
Revised Date: 14 September 2023
Accepted Date: 20 September 2023
Available Online: 21 September 2023

Figures(4)

Glycosyl radicals, produced under mild photoredox conditions, show unique utility in the preparation of C-linked glycoconjugates. We herein report the construction of C-glycosidic bonds on α,β-dehydroalanine (DHA) of peptides with easily available glycosyl bromides as glycosyl radical precursors under highly anomeric control, leading to C-glycosylation modifications of peptides. This method not only has outstanding functional group compatibility, but also is feasible in near-physiological conditions (pH ~ 7 and temperature T ≤ 37 ℃ in aqueous media).
- Glycosylation,
- C-Glycosides,
- Glycopeptides,
- Dehydroalanine,
- Photoredox catalysis
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